rac-Ethyl 4-(4-(benzyloxy)-3-methoxyphenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA2385915

Max Phase: Preclinical

Molecular Formula: C23H26N2O5

Molecular Weight: 410.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(CC)NC(=O)NC1c1ccc(OCc2ccccc2)c(OC)c1

Standard InChI:  InChI=1S/C23H26N2O5/c1-4-17-20(22(26)29-5-2)21(25-23(27)24-17)16-11-12-18(19(13-16)28-3)30-14-15-9-7-6-8-10-15/h6-13,21H,4-5,14H2,1-3H3,(H2,24,25,27)

Standard InChI Key:  MNARIJUQEZQKAI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    5.4271  -24.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1410  -24.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8562  -24.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8528  -25.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5670  -26.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2819  -25.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2780  -24.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5631  -24.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5575  -23.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8402  -23.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9976  -26.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9962  -26.9975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7078  -27.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4235  -26.9968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4231  -26.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7070  -25.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7070  -28.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1378  -25.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7066  -24.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4209  -24.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9918  -24.5187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1356  -24.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7121  -24.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131  -23.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988  -23.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839  -23.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879  -24.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0027  -24.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8498  -24.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520  -26.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  8  9  1  0
  9 10  1  0
 11  6  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 13 17  2  0
 15 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
  1 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 22 29  1  0
 18 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385915

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 410.47

Molecular Weight (Monoisotopic): 410.1842

AlogP: 3.86

#Rotatable Bonds: 8

Polar Surface Area: 85.89

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.56

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -0.76

References

1. Dubernet M, Duguet N, Colliandre L, Berini C, Helleboid S, Bourotte M, Daillet M, Maingot L, Daix S, Delhomel JF, Morin-Allory L, Routier S, Walczak R..  (2013)  Identification of New Nonsteroidal RORα Ligands; Related Structure-Activity Relationships and Docking Studies.,  4  (6): [PMID:24900700] [10.1021/ml300471d]

Source

Source(1):

• Scientific Literature